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CAS No. : | 88075-18-7 | MDL No. : | MFCD20257321 |
Formula : | C11H14OSi | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GCOHQMFWLBOIHL-UHFFFAOYSA-N |
M.W : | 190.31 | Pubchem ID : | 10750210 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.27 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 58.69 |
TPSA : | 20.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.79 cm/s |
Log Po/w (iLOGP) : | 2.67 |
Log Po/w (XLOGP3) : | 3.76 |
Log Po/w (WLOGP) : | 2.7 |
Log Po/w (MLOGP) : | 2.96 |
Log Po/w (SILICOS-IT) : | 1.39 |
Consensus Log Po/w : | 2.7 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.73 |
Solubility : | 0.0354 mg/ml ; 0.000186 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.88 |
Solubility : | 0.0252 mg/ml ; 0.000133 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.17 |
Solubility : | 0.128 mg/ml ; 0.000671 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 24 h; Inert atmosphere | 4-Iodophenol 9 (2 g, 9.09 mmol, 1 eq) were dissolved in 20 mL of dry toluene. To the resulting solution PdCl2(PPh3)2 (191.4 mg,0.27 mmol, 0.03 eq), copper (I) iodide (172.8 mg, 0.909 mmol, 0.1 eq), N,N-diisopropylethylamine (1.58 mL, 9.09 mmol, 1 eq) and trimethylsilylacetylene (1.28 mL, 9.09 mmol, 1 eq) were subsequently added. The reaction was stirred at room temperature for 24 h. Evaporation of the solvent, and the residue was purified by column chromatography (EtOAc/hexane = 1:10) to afford 10 (1.73 g, quant.) as a brown oil. 1H-NMR (CDCl3, 500 MHz) δ 7.37 (2H, d, J= 8.8 Hz, Ar-H), 6.76 (2H, d, J = 8.8 Hz, Ar-H), 4.92 (1H,brs, Ar-OH), 0.24 (9H, s, -Si(CH3)3). 13C-NMR (CDCl3, 75MHz) δ 155.76, 133.69, 115.49, 115.31, 105.02, 92.50, 0.05. |
100% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N,N-diethylnmethylamine In N,N-dimethyl-formamide at 60℃; for 0.333333 h; Microwave irradiation; Inert atmosphere | 4-Iodophenol (2) (440 mg, 2.0 mmol) and trimethylsilylacetylene(0.42 mL, 3.0 mmol) were dissolved in 10 mL ofdiethylmethylamine and 10 mL of dimethylformamide,and then, 60 mg (0.30 mmol) of CuI and 70 mg (0.10 mmol)of PdCl2(PPh3)2 were added. The solution was stirred in amicrowave reactor at 60 °C for 20 min (100 W) under N2atmosphere. The solvent was evaporated, and the residuewas dispersed in 20 mL aqueous 2 M HCl and extractedwith diethyl ether (3 × 20 mL). The combined organic layers were dried over Na2SO4, the solvent was evaporated,and the residue purified with FCC (isohexane-ethylacetate 3:1) to give 380 mg (100 percent) of 4 as a brown oil.– 1H NMR (400 MHz, CDCl3): δ = 0.23 (s, 9 H, 3 CH3), 6.76(d, J = 8.8 Hz, 2 H, aromat. CH), 7.34 (d, J = 8.8 Hz, 2 H,aromat. CH). – 13C NMR (125 MHz, CDCl3): δ = 0.19 (3 CH3),92.12 (quat. C), 105.39 (quat. C), 114.98 (quat. C), 115.48(2 aromat. CH), 133.51 (2 aromat. CH), 156.44 (quat. C).These data are in accordance with those published inRef. [12]. – GC-MS (EI): m/z (percent) = 190 (23) [M]+, 175 (100).– HRMS: m/z = 190.0814 (calcd. 190.0815 for C11H14O2Si,[M]+). – IR (KBr): ν (cm−1) = 3322, 2959, 2155, 1662, 1607,1508, 1437, 1251, 1230, 1167, 1100, 867, 840. |
80% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 25℃; for 24 h; | A mixture of 4-iodophenol (3.08 g, 14.0 mmol), trimethylsilylacetylene (2.1 mL, 15.2 mmol), PdCl2(PPh3)2 (31 mg, 0.044 mmol), and CuI (4.9 mg, 0.026 mmol), NEt3 (10 mL) in THF (20 mL) was stirred at 25 °C. After stirring for 1 day, to the mixture was added aqueous 2 M HCl, and extracted with EtOAc (3 times). The organic phase was sequentially washed with brine, aqueous sat.NaHCO3, and brine, and dried with MgSO4. After concentration, the residue was purified with silicagel column chromatography (hexane to hexane/EtOAc = 8/2) to afford 4-(trimethylsilylethynyl)phenol as colorless amorphous solids (2.12 g, 80percent). mp 41-42 °C (colorless amorphous solids, recrystallized from hexane); Rf: 0.40 (hexane/EtOAc = 4/1); 1H NMR (CDCl3, 400 MHz): ;0.24 (s, 9H), 5.23 (s, 1H), 6.76 (d, 2H, J = 8.8 Hz), 7.36 (d, 2H, J = 8.8 Hz); 13C NMR (CDCl3, 100 MHz): 0.0, 92.5, 105.0, 115.3, 115.5, 133.7, 155.8; IR (KBr): vmax 3745, 3334, 2958, 2898, 2158, 1886, 1606, 1508, 1437, 1358, 1252, 1209, 1168, 1101, 866, 839 cm-1; HRMS (DART): M+ calcd for C11H14OSi, 190.08139; found, 190.08161 |
79% | at 80℃; for 24.5 h; Inert atmosphere | To a refluxingsuspension of iodophenol (2.5 g, 1.0 mmol), copper acetate monohydrate (1.35 g,1.07 mmol), and palladium chloride (1.8 g, 1.07 mmol) in triethylamine (10 mL) in an inertatmosphere was added dropwise trimethylsilylacetylene (1.36 g, 1.20 mmol) over 30 min.The reaction mixture was further refluxed at 80C for 24 h under nitrogen atmosphereand monitored by TLC for completion of reaction. The mixture was cooled and filteredto remove the solids. The volatile solvents were evaporated under reduced pressure, andthe resulting crude light brown colored viscous oil was extracted into ether, washed withsaturated potassium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated.The silylated product was purified by column chromatography on silica gel with3percent ethyl acetate in hexane as eluent. Yield = 1.58 g (79percent). |
68% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; | A suspension of 4-iodophenol (3.00 g, 13.64 mmol), ethynyltrimethylsilane (2.27 mL, 16.36 mmol), copper (_) iodide (130 mg, 0.68 mmol), bis(triphenylphosphine)palladium(II) dichloride (479 mg, 0.68 mmol), TEA (5.70 ml, 40.91 mmol) were stirred in THF (23 mL) at ambient temperature for overnight. The reaction solvent was evaporated under reduced pressure, and the residue was purified by column chromatography with hexane/ethyl acetate (2/1, v/v) to obtain the compound 52 (1.76 g, 68percent yield): 1H NMR (400 MHz, CDCl3) _ 7.33 (d, J = 8.7 Hz, 2H), 6.72 (d, J = 8.7 Hz, 2H), 5.82 (bs, 1H), 0.23 (s, 9H); 13C NMR (100 MHz, CDCl3) _ 155.8, 133.8, 115.6, 115.4, 105.6, 92.9, 0.1. |
40.5% | Stage #1: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran for 0.333333 h; Inert atmosphere Stage #2: for 21 h; Reflux |
Compound 1 was obtained as shown in Scheme I shown below.That is, p-iodophenyl (9.90 g, 45.0 mmol), copper (I) iodide (CuI (I)) (0.358 g, 1.8 mmol)Bis (triphenylphosphine) palladium (II) dichloride (PdCl 2 (PPh 3) 2) (0.640 g, 0.90 mmol)Was substituted with deaerated argon (Ar), then tetrahydrofuran (THF) (112.5 mL) and triethylamine (Et 3 N) (7.5 mL) were added and the mixture was stirred for 20 minutes. Thereafter, trimethylsilylacetylene (TMSA) (6.35 mL, 45.0 mmol) was added and the mixture was shaken for 21 hoursFollowed by stirring (refluxing). After completion of the reaction, the solvent was distilled off, diethyl ether was added to the residue, and the obtained organic layer was washed with pure water and dried with anhydrous magnesium sulfate. After removing the anhydrous magnesium sulfate by filtration, the solvent was distilled off to obtain a brown viscous residue.The obtained residue was dissolved in benzene (20 mL), heated to 60 ° C., and ethylenediamine (4 mL) was added and the mixture was stirred for 20 minutes. The precipitate was filtered off and the filtrate taken out was washed with 0.5 M aqueous hydrochloric acidWashed with the solution and dried over anhydrous magnesium sulfate. After anhydrous magnesium sulfate was filtered off, The solvent was distilled off and the residue was purified by silica gel column chromatography (eluent: ethylacetone / hexane = 1/4)Compound 1 (3.47 g, yield: 40.5percent) was obtained as a brown solid. Identification of Compound 1 was carried out by 1 H-NMR spectrum. Incidentally, 1 H-NMRPector was measured after dissolving Compound 1 in deuterochloroform without tetramethylsilane (TMS). |
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